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Real Estate Matchmaker

Ash Gailey

She creates meaningful connections between buyers, sellers, homes, and opportunities, bringing strategy, creativity, and genuine care to every real estate journey.

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Where Possibilities Connect

From finding a home to discovering your next opportunity, thoughtful guidance helps bring the right pieces together.

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Meet Ash

Global Real Estate Advisor

I have always believed that real estate is about people first. Homes are personal, and the right home can change the way you experience your life. That is why I call myself a Luxury Real Estate Matchmaker. I am here to make meaningful connections between buyers, sellers, homes, and opportunities, whether that connection happens here in St. Augustine or somewhere across the world.

My background is a little different from the traditional real estate path, and I believe that is one of my greatest strengths.

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Featured Properties

Explore a selection of properties that stand out for their character, possibilities, and potential to be the right match.

2125 W LOU Drive
For Sale

2125 W LOU Drive

3 Beds | 2 Baths | 1,232 Sq.Ft.
$299,900
25 LINDA MAR Drive, St. Augustine
For Sale

25 LINDA MAR Drive, St. Augustine

3 Beds | 3 Baths | 1,822 Sq.Ft.
$859,000
42 PALMER NORTH LOT 4&6 Street NORTH LOT 4&6, St. Augustine Unit: NORTH LOT 4&6
For Sale

42 PALMER NORTH LOT 4&6 Street NORTH LOT 4&6, St. Augustine Unit: NORTH LOT 4&6

| 420 Sq.Ft.
$565,000
42 PALMER Street SOUTH LOT 5, St. Augustine Unit: SOUTH LOT 5
For Sale

42 PALMER Street SOUTH LOT 5, St. Augustine Unit: SOUTH LOT 5

| 2 Baths | 474 Sq.Ft.
$365,000
42 PALMER Street, St. Augustine
For Sale

42 PALMER Street, St. Augustine

| 429 Sq.Ft.
$695,000
6631 WELLINGTON PLACE Lane
For Sale

6631 WELLINGTON PLACE Lane

2 Beds | 2 Baths | 1,083 Sq.Ft.
$225,000
541 VILLAGE GRANDE Drive
For Sale

541 VILLAGE GRANDE Drive

5 Beds | 4 Baths | 3,238 Sq.Ft.
$1,150,000
289 PALM BREEZE Drive
For Lease

289 PALM BREEZE Drive

4 Beds | 3 Baths | 2,391 Sq.Ft.
$4,500
76 PARK CENTER Avenue
For Lease

76 PARK CENTER Avenue

2 Beds | 2 Baths | 1,614 Sq.Ft.
$3,300
168 LAUREL Lane
For Sale

168 LAUREL Lane

3 Beds | 2.5 Baths | 2,166 Sq.Ft.
$1,499,000
4999 ALTA VISTA Avenue, St. Augustine
For Sale

4999 ALTA VISTA Avenue, St. Augustine

3 Beds | 3.5 Baths | 1,864 Sq.Ft.
$1,125,000
299 APPALOOSA Avenue, St. Augustine
For Sale

299 APPALOOSA Avenue, St. Augustine

4 Beds | 3 Baths | 2,960 Sq.Ft.
$699,000
1048 INGLESIDE Avenue
For Lease

1048 INGLESIDE Avenue

4 Beds | 3 Baths | 2,056 Sq.Ft.
$2,800
1048 INGLESIDE Avenue
For Sale

1048 INGLESIDE Avenue

3 Beds | 3 Baths | 1,936 Sq.Ft.
$415,000
95179 WILD CHERRY Drive
For Sale

95179 WILD CHERRY Drive

4 Beds | 3 Baths | 2,499 Sq.Ft.
$1,175,000
3558 DERBY FOREST Drive
For Sale

3558 DERBY FOREST Drive

4 Beds | 2 Baths | 1,856 Sq.Ft.
$315,000
156 TWILIGHT Lane, St. Augustine
For Sale

156 TWILIGHT Lane, St. Augustine

4 Beds | 2.5 Baths | 2,450 Sq.Ft.
$595,000
208 SEAFORTH Drive, St. Augustine
For Sale

208 SEAFORTH Drive, St. Augustine

4 Beds | 2 Baths | 2,126 Sq.Ft.
$517,000
252 UNION HILL Drive
Active Under Contract

252 UNION HILL Drive

4 Beds | 3 Baths | 2,082 Sq.Ft.
$624,900
2524 WHISPERING WOODS Boulevard 3
For Sale

2524 WHISPERING WOODS Boulevard 3

3 Beds | 2 Baths | 1,128 Sq.Ft.
$260,000
1372 EAGLE CROSSING Drive
For Sale

1372 EAGLE CROSSING Drive

6 Beds | 4 Baths | 3,132 Sq.Ft.
$560,000
1855 MOORINGS Circle
For Sale

1855 MOORINGS Circle

5 Beds | 4 Baths | 3,726 Sq.Ft.
$689,000
714 CURVED BAY Trail
For Sale

714 CURVED BAY Trail

3 Beds | 3.5 Baths | 2,770 Sq.Ft.
$1,150,000
1702 BALBOA Lane
For Sale

1702 BALBOA Lane

3 Beds | 1 Baths | 1,440 Sq.Ft.
$272,450
206 WILLOW OAK Way
Pending

206 WILLOW OAK Way

3 Beds | 3 Baths | 3,025 Sq.Ft.
$1,299,000
70 SPOONBILL Circle, St. Augustine
Active Under Contract

70 SPOONBILL Circle, St. Augustine

2 Beds | 2 Baths | 1,798 Sq.Ft.
$389,900
233 WOODGATE Drive
For Sale

233 WOODGATE Drive

3 Beds | 2 Baths | 1,967 Sq.Ft.
$615,000
11839 CHARLIE Road
For Sale

11839 CHARLIE Road

4 Beds | 2 Baths | 1,993 Sq.Ft.
$365,000
1688 SUSAN Drive
For Sale

1688 SUSAN Drive

3 Beds | 2 Baths | 1,701 Sq.Ft.
$267,500
556 FOX HOLLOW Lane, St. Augustine
For Sale

556 FOX HOLLOW Lane, St. Augustine

3 Beds | 2 Baths | 1,421 Sq.Ft.
$379,999
1294 INGLESIDE Avenue
Active Under Contract

1294 INGLESIDE Avenue

4 Beds | 2 Baths | 1,645 Sq.Ft.
$525,000
309 ELZA Lane, St. Augustine
For Sale

309 ELZA Lane, St. Augustine

4 Beds | 2.5 Baths | 2,400 Sq.Ft.
$709,000
145 WHISPERING OAKS Circle, St. Augustine
For Sale

145 WHISPERING OAKS Circle, St. Augustine

3 Beds | 2 Baths | 1,859 Sq.Ft.
$795,000
76 PARK CENTER Avenue
For Sale

76 PARK CENTER Avenue

2 Beds | 2 Baths | 1,614 Sq.Ft.
$525,000
10948 INDIES Drive S
For Sale

10948 INDIES Drive S

4 Beds | 2 Baths | 1,368 Sq.Ft.
$275,000
2895 PLAINWOOD Place
For Sale

2895 PLAINWOOD Place

4 Beds | 3 Baths | 2,261 Sq.Ft.
$370,000
29 PRAIRIE Lane
For Sale

29 PRAIRIE Lane

4 Beds | 2 Baths | 1,865 Sq.Ft.
$325,000
2646 ANNISTON Road
Active Under Contract

2646 ANNISTON Road

4 Beds | 2 Baths | 1,777 Sq.Ft.
$360,000
659 SEAGROVE Drive
Active Under Contract

659 SEAGROVE Drive

6 Beds | 6 Baths | 4,905 Sq.Ft.
$1,749,000
105 MIDDLETON Place
For Sale

105 MIDDLETON Place

3 Beds | 4.5 Baths | 5,788 Sq.Ft.
$2,900,000
416 AMECA Avenue
For Sale

416 AMECA Avenue

3 Beds | 2 Baths | 1,440 Sq.Ft.
$299,000
2608 SACK Drive E
Active Under Contract

2608 SACK Drive E

5 Beds | 2 Baths | 1,791 Sq.Ft.
$339,000
8508 LONG MEADOW Court
For Sale

8508 LONG MEADOW Court

4 Beds | 2.5 Baths | 2,224 Sq.Ft.
$310,000
109 CARRIAGE Court
For Sale

109 CARRIAGE Court

5 Beds | 5 Baths | 4,250 Sq.Ft.
$4,240,000
978 ROOSTER HOLLOW Way
For Sale

978 ROOSTER HOLLOW Way

5 Beds | 3 Baths | 3,695 Sq.Ft.
$565,000
428 NEPTUNE Road
For Sale

428 NEPTUNE Road

3 Beds | 2 Baths | 1,002 Sq.Ft.
$225,000
10286 DRIFTWOOD HILLS Drive
For Sale

10286 DRIFTWOOD HILLS Drive

3 Beds | 2 Baths | 1,215 Sq.Ft.
$259,000
815 S 11TH Avenue S
For Sale

815 S 11TH Avenue S

4 Beds | 3.5 Baths | 2,800 Sq.Ft.
$1,250,000
192 TWELVE OAKS Lane
For Sale

192 TWELVE OAKS Lane

4 Beds | 5 Baths | 4,360 Sq.Ft.
$2,499,000
328 PALOS Court, St. Augustine Shores
Pending

328 PALOS Court, St. Augustine Shores

2 Beds | 1.5 Baths | 1,215 Sq.Ft.
$1,725
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Discover Where You Could Live

Get a closer look at the neighborhoods, lifestyles, and local details that can help you find the right match.

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St. Augustine

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St. Augustine Beach

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St Johns

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Ponte Vedra Beach

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Palm Coast

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Flagler Beach

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Jacksonville

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Vilano Beach

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Matching buyers and sellers globally and turning homes into love stories

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The Right Match Changes Everything

As a Luxury Real Estate Matchmaker, she brings together people, properties, and opportunities with a personal approach shaped by construction experience, business strategy, creativity, and genuine care for every client.
Let's Connect

Contact Details

Ash Gailey

Phone

386.237.3318

Email

[email protected]

Address

81 King St St Augustine, FL 32084

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